


I'll Watch Over You

by SomethingBlue42



Series: Suptober 2020 [8]
Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Anal Fingering, Anal Sex, Angst and Porn, Barebacking, Blow Jobs, Bottom Dean Winchester, Bottom Demon Dean Winchester, Castiel Deserves Better (Supernatural), Castiel Drives the Impala (Supernatural), Castiel Loves Dean Winchester, Come as Lube, Dark Dean Winchester, Dead Sam Winchester, Dean Winchester Being an Asshole, Demon Dean Winchester, Emotional Hurt, Emotionally Hurt Castiel (Supernatural), Hurt No Comfort, M/M, Mark of Cain (Supernatural), Multiple Partners, Past Dean Winchester/Other(s), Sex in/on the Impala (Supernatural), The Impala (Supernatural), Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-10-19
Updated: 2020-10-19
Packaged: 2021-03-08 23:48:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,095
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27095329
Author URL: https://archiveofourown.org/users/SomethingBlue42/pseuds/SomethingBlue42
Summary: Suptober Day 8: Heartless"And when you finally turn – and you will turn – Sam and everyone you know, everyone you love – they could be long dead. Everyone except me. I'm the one who will have to watch you murder the world."
Relationships: Castiel/Dean Winchester, demon dean winchester/Castiel
Series: Suptober 2020 [8]
Series URL: https://archiveofourown.org/series/1960396
Comments: 4
Kudos: 79





	I'll Watch Over You

The day the Impala turns 100, Castiel is pulling Dean out of a strip club before the altercation with the bouncers can turn into an all-out brawl. Dean is spry for a man of 89, not looking a day over 33, but then again, he's becoming less and less "man" as the years pass.

The mark on his forearm burns, scorching under Castiel's palm as he drags Dean towards the Impala. Dean eventually jerks out of Castiel's grasp and digs a hand in his pocket for the keys but finds them empty. Castiel pulls them out of his trench and offers them over.

"Nah, you drive."

Castiel blinks at Dean, at the Impala, and then back again. "Are you-"

"Come on, bud. We gotta clear 4 states to get back to the bunker and Candy in there got my last $40." Dean shrugs his shoulders. "So unless you wanna pay for the room on your back-" Dean's eyes flicked over Castiel's form licking his lips, "-one of us is going to have to drive all night."

Dean reaches for the back door on the driver's side, yanking it so that it clunks into the side of the truck next to it. "DEAN!" Castiel snaps, hand gripping his bicep, and Dean rolls his eyes, flicking a hand.

"It's just a car, Cas. I'm fucking tired."

Castiel blinks at him, mouth popping open as Dean crawls into the backseat, flopping onto his back and getting comfortable. Castiel closes his mouth as he closes the door, fingertips brushing over the knick in the paint, and it disappears.

It's been decades, and Castiel still can't get used to it. The black eyes and the mean streak he's learned to live with, and there are parts he even enjoys. When Dean was human, there were too many emotions and biases he couldn't get past. Now Dean's only concern is what can bring him the most pleasure. Sometimes it's drinking an entire bar out of its top-shelf liquor. Sometimes it's starting a brawl. And sometimes it's shoving Castiel's face into a scratchy motel pillow and taking him with his wrists held in a vice-like grip at his lower back, unable to resist, not that Castiel ever really wanted to.

But the devil-may-care attitude towards the Impala just doesn't sit right. Castiel is responsible for her now though Dean still enjoys driving her, too fast, and often with little care for others on the road. "It ain't like whatever happens we ain't gonna walk away from it," Dean had said after a near-miss with a mini-van chauffeuring half a little league team. Dean's eyes had flashed black. "Perk of immortality am I right Angel?"

Castiel pulls onto the highway and heads west, deeper into the night. He remembers nights like this, half a century ago, himself in the backseat with Dean behind the wheel and Sam riding shotgun, silent aside from the barely audible warble of the radio. Sam's been dead ten years now. His ashes were still smoldering when Dean clapped Castiel on the shoulder and said he was meeting a girl and not to wait up.

Castiel glances in the back seat, finding Dean sprawled out, eyes closed, and for a moment, Castiel can pretend they're on their way back from a hunt. He can watch Dean in the rearview, face relaxed and almost innocent in sleep, and remember watching over him at the very beginning, walking his dreamscape to banish the nightmares away. 

Demons don't dream. When Castiel's grace reaches for Dean's scarred soul, it seems to recoil with a hiss, and Dean's face crumples in displeasure, wiggling against the seat.

"Dammit, I told you not to _do_ that. Shit hurts." Dean grouses, and Castiel mumbles an apology.

The miles tick by in silence, just the sound of the wind and the rumble of a v8 engine echoing across the plains. Castiel doesn't get tired, crossing state line after state line while the sun begins to chase them west. Castiel lets his hands skim over the steering wheel, holding it loosely to feel the worn leather. The memory of Dean's hands doing the same thing, one falling to his lap as the other hung over the top of the wheel while the young man turned his head to look at Castiel in the passenger seat, green eyes shining in the dashboard light, grinning at his own joke.

"You're thinkin' really loud up there, Angel."

Castiel sits up straighter in his seat, eyes firmly on the road, but he can hear Dean shifting around in the backseat, the squeak of vinyl, and his low groan as he pulls himself upright. Castiel feels him at his shoulder, Dean leaning forward, resting his elbows on the seatback in front of him, folding his hands. Castiel glances down, the Mark standing out angry and red on his forearm. Dean's lips brush the shell of Castiel's ear.

"If you could go back would you?" Dean queries his voice light, almost a taunt, and Castiel's fingers tighten around the wheel.

"In a heartbeat."

Dean's chuckle is warm against Castiel's neck. "Even if it meant that Dean never got over his gay panic." Dean's voice dips lower. "Never got up the courage to even hold your hand much less fuck you like I do."

Castiel swallows thickly. "Yes."

"Even if it meant burning up this beautiful body you spent so much time reconstructing right along on that pire with Sammy?"

Castiel's eyes harden. "Yes."

Dean's laugh is low and mean as he presses his nose against Castiel's pulse point. "You're so sad, Angel." One large hand comes up to encircle Castiel's throat, his palm pressing against Castiel's adam's apple hard enough to hurt. "You know what that does to me..."

Castiel's fingers grip the wheel hard as Dean's lips attach to his neck, a large hand sliding down the middle of his chest to cup him between his legs.

"Dean…" Castiel's voice is a warning, eyes fluttering as the heel of Dean's hand grinds into his lap, his teeth snagging on Castiel's earlobe.

"Pull over."

Castiel rolls his eyes, but his hips shift under Dean's hand. "We're almost to the bunker."

Castiel lets out a sharp cry as Dean's grip becomes painfully tight for a split second. "You know I don't like to wait." Castiel hisses as Dean's teeth sink into the side of his neck hard. "Pull over."

Castiel sets his jaw, eyes steady on the two-lane road in front of him. "No."

Dean huffs an annoyed sigh, falling back against the seat and Castiel breathes one of relief. Until he hears the sound of Dean's belt buckle jingling. Castiel's eyes flick to the rearview mirror and widen as he watches Dean's head tip back, biting his bottom lip hard. Castiel's hand shakes as he reaches to adjust the mirror, and his mouth goes dry as he sees Dean's hand stroking slowly up and down his hard length. 

"See something you like, Angel?"

Castiel's eyes jump to Dean's in the mirror, finding one of his large hands shucking up his t-shirt to reveal the toned stomach he could never seem to maintain as a human, thumbing one nipple and making himself gasp. A low moan rumbles in his chest, head falling back again, and his hand stops, squeezing tight at the base of his shaft. In the growing dawn, Castiel watches a bead of precum bubble at the head and dribble down the underside of the shaft.

"Pull. Over."

Castiel shifts in his seat, voice weak. "We're fifteen minutes away."

"Mmmm. If you pull over right now…" Dean's head lifts, green eyes meeting blue in the mirror. "I'll let you fuck me."

Castiel's foot slips off the gas pedal, and the Impala slows noticeably, making Dean chuckle and begin his slow strokes again. Castiel shakes his head and lifts his foot to return it to the pedal. 

"You've wanted that for a long time haven't you?" Castiel is going to put his foot back on the gas now. Any moment. "You want to feel me come on your dick. Beg for it. Scream your name."

Cas can swear up and down that he meant to punch the gas and missed, hitting the brake instead, but the lie is ridiculous even to his own ears. He tries not to think as he slides to the side of the road and puts the Impala in park, killing the headlights. Castiel gasps when he turns to look back and finds Dean right there, eyes black.

"Get back here."

Strong hands grip his shoulders and rip him over the seatback into the backseat. In a whirlwind of nails, skin, and teeth, he's on his back half-naked with Dean between his legs, dragging his pants and boxers down his thighs. Castiel's head cracks back against the window as Dean takes all of him in a single bob of his head, nose nuzzling against the soft down of hair at the base of his shaft. His hand slaps the seatback when Dean swallows around him, throat contracting around the head of his dick in intense pulses. 

Dean pulls back, lower teeth grazing the underside of Castiel's shaft in a blur of pleasure and pain that makes Castiel whimper, hands threading back into Dean's hair. "You wanna fuck my mouth, don't you?" 

Dean's lips are puckered against the head of his cock, pressing warm, wet kisses into the spongy tip as his green eyes sparkle with mischief, and Castiel can only nod. Dean's hands slide under Castiel's hips, gripping handfuls of his ass and encouraging him to thrust up into his mouth. Castiel allows himself to become lost in it, one hand cupping the back of Dean's neck while his other combs back through his hair, guiding him gently up and down. Dean hums and moans around him, opening his throat and letting Castiel press him all the way down. Castiel's eyes roll back in his head, hips pushing up harder and faster at the feel of Dean's plush lips vibrating against his skin. 

Castiel's legs widen when he feels spit slick fingers press between his cheeks, the tight ring of his entrance fluttering as Dean strokes him there. Dean's head tips, sucking sweetly at the head as the tips of his fingers breach Cas' hole.

"Is this what you want to do to me?" Castiel's back arches as one thick digit presses in to the knuckle, pausing to enjoy the clench of Castiel's body before sinking all the way in to the hilt. "Are you going to stretch me open like this? Get me ready?"

Castiel's head bobs, combing his fingers back through Dean's hair, petting him, and tugging his mouth down again. Dean obliges with a smirk, tonguing the slit and teasing the crown as his finger works deeper before adding another, and Castiel's hips are trying to press down into his hand and up into his mouth at the same time.

"Are you ready for me, Angel?"

Castiel's eyes open to find Dean lifting to his knees, body on full display as the rising sun streams through the back window. He's stroking himself slowly, and Castiel's hands fly to his hips, blue eyes fixing on how his own cock is straining up between Dean's legs, begging for his hole. Castiel's fingers trail over Dean's hip, brushing against his balls and making the other man shiver as Castiel reaches behind.

Castiel's brows furrow as his fingertips meet slick flesh, fingertips pressing lightly and slipping past Dean's entrance without resistance. Dean lets out a soft scoff that turns into a chuckle when Castiel's eyes meet his. Dean leans over, planting a hand on the door near Castiel's shoulder, licking his lips as he contemplates Castiel's face.

"Now you've ruined the surprise." Castiel blinks at him, dread curling in his belly as Dean leans in, nose nuzzling against his. "That's from the guy I let fuck me raw in the bathroom while you were enduring the lap dance I bought you."

Dean pulls back just enough to see the horror and hurt spread across Castiel's face, his own twisting in malicious glee as he shoves Castiel's hand aside and impales himself on Castiel's dick. Dean's head falls back, a low moan pulling from his throat. Castiel feels tears sting the corners of his eyes, disappointment bitter as bile in the back of his throat. Dean's arms lock behind him, hands gripping Castiel's thighs as he began to bounce savagely on his lap, the pleasure of it barely breaking through the hurt. 

"What's wrong, Angel?" Dean asks breathlessly, hips swiveling in small circles, his eyes flashing black. "Isn't this what you always wanted?"

Castiel's head falls to the side, eyes closing, unable to look at him. He feels Dean's hand curl around his chin before fingers bite hard into his cheeks, forcing Castiel to look up at him again. Dean shifts forward, rolling his hips in a way that makes Castiel's eyelids flutter despite himself, his vessel warring with his grace, and he reaches for Dean, hand slipping around his leaking cock quickly. Dean gasps as Castiel begins to jerk him in swift, rough strokes, twisting his wrist at the end, and Dean starts to bounce against him again. 

"Fuck," he moans lowly, his head falling back, and Castiel grits his teeth, making a tight circle of his thumb and forefinger and giving short quick strokes just under the head and over it, ready for this to be over. Dean sucks in a great breath, his eyes flying open as his mouth forms a perfect "o" head tipped back. "Fuck. Oh fuck. Mmmm." 

Dean tucks his head back down, planting his hands against Castiel's chest, and grinds against him, trying to widen his legs to take more of him in. He blurs in Castiel's vision as the tears threaten again, bitter as the vision he's so longed to see is tainted with the knowledge that Dean had done this just to hurt him, that the thing that he was now did it for fun. 

"Oh god. Oh…" Dean's back arches and Castiel watches his hips stutter, his stomach heaving as Castiel begins the swift, sure strokes again. Dean's face crumples, bracing a hand on Castiel's shoulder as he leans closer, breath fanning Castiel's face. Dean's voice is weak as he breathes, "Cas…"

Castiel's eyes snap up, and his heart surges, finding green eyes pleading with his. Deep down, he knows it won't last, understands that right then, so close to orgasm, Dean can't focus on the game or anything else but chasing his pleasure. It is the closest Castiel ever sees to the man he'd pulled out of hell, the man he'd fallen in love with but is gone now, never having gotten the chance to love him back. 

Castiel does his best to suspend Dean there, on the verge of coming, his strokes measured, pushing his hips up into Dean to nudge against his prostate, making Dean wail as he drops his forehead against Castiel's. Castiel watches Dean's face, watches him fall apart as he finally wrings the orgasm from Dean's body. His free hand falls against the scar curling around Dean's bicep, his own release pulsing through him, more relieved that it's over than satisfied in pleasure. 

Dean shifts over him, letting out a sharp "woo" before his head tips back, and he chuckles deeply. "Damn, Angel. Where you been hiding that, huh?" Dean leans down to kiss him. Castiel turns his head away, eyes closing. "Aw don't be like that." Dean murmurs against his cheek, kissing him there and then up his jaw to kiss at his ear. "It didn't mean anything."

Castiel cuts his eyes up at Dean, who smirks at him, nuzzling his nose before pressing a deep kiss to his lips. His tongue slides against Castiel's, hand delving into the hair at Castiel's crown, so Castiel ends up lost in it, sighing when he softens enough to slip out as Dean sucks deep hickeys onto his neck, but he doesn't care at the moment. Dean's nose nuzzles at his pulse point, breath warm on Castiel's ear.

"Granted this didn't mean anything either..."

Castiel growls, glaring as Dean pulls back, a ruthless smile on his face. Before Castiel can think, his hand on Dean's bicep tightens, and a strangled whine pulls in Dean's throat, trying to shake him off. Castiel's hand burns and Dean scowls at his had over the offensive scar. Dean's face pales, staring down into the blue glow of Castiel's grace-filled eyes.

"Angel… hey… hey… none of that now." Dean's eyes flash black, a hand closing over Castiel's wrist, and the blue glow dies down. "You can't smoke me out. I'll die." Dean's hand cups Castiel's cheek, eyes still just two black holes in his beautiful face. "And then you'd be all alone." Dean clicks his tongue, and a shiver of fear works its way down Castiel's spine. He lets go and falls dejectedly back against the door. 

The sun has fully risen now as Dean pulls his jeans back on, not bothering with underwear or even buttoning them before climbing out and rounding the front to slide into the driver's seat. He adjusts his mirrors, canting the review down to see Castiel. Dean smirks. 

"'Ey, Cas?" 

Castiel closes his eyes, feeling the bump as the Impala trundles back onto the road. "Yes, Dean?"

"D'you know what today is?" Dean turns in his seat to peer back at Castiel, who still hasn't moved. "It's Baby's birthday!" Dean revvs the engine making her lurch forward, and Castiel has to brace his hand against the front seat to not roll to the floorboard.

"Actually it was yesterday." Castiel sighs, reaching to pull his own pants up, a wave of his hand banishing the mess on the seat below him. Dean snorts as Castiel sits up, glaring at him in the rearview.

"Close enough. Whaddaya say we stop at iHop? Get some of them birthday cake pancakes and celebrate?" 

Castiel looks up, seeing Dean's raised eyebrows in the mirror, green eyes sparkling, and Castiel can almost pretend if he focuses really hard and avoids the empty passenger seat in his peripheral that it's the morning after a hunt. That Sam is still alive and young, snorting as if to say _Pancakes? Again, Dean?_ but says nothing, and Castiel's nod of assent is all they need for Dean to break out into a wide grin, give a howl of pleasure and really open her up to let Baby run.

**Author's Note:**

> Reviews/Kudos are <3
> 
> [Visit me on Tumblr](https://desti-feeels.tumblr.com)   
> 


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